Explore Longboat Key

With warm weather year-round and some of the best beaches in the region, Longboat Key has become one of the premiere vacation destinations in the Florida area. Longboat Key has several major festivals and events held throughout the year, so try to plan your trip around one of them. Some of the major events in the area include the St. Armand's Circle Art Festival, held in late January; the Say I Do Again Festival on Valentine's Day, where couples can renew their vows on Siesta Public Beach; and the Siesta Fiesta, an annual arts and crafts fair held in early May.

While you're on vacation in the Longboat Key area, be sure to make time for some of these main attractions and destinations:

-Sarasota Jungle Gardens: There are five shows at the gardens that feature both animals and rare plants.

-Historic Palm Avenue: This is known as downtown Sarasota's "Best Walk in Town."

-Bolletieri Tennis Academy: Located in nearby Bradenton, see the academy where champions like Andre Agassi and Monica Seles got their start.

-Go shopping: St. Armand's Circle has a huge selection of unique shops and fine dining.

-Catch a baseball game: If you're in the area during the spring, the Baltimore Orioles train in nearby Sarasota.

-Historic Spanish Point: Take a guided tour here and learn more about the history of Southwest Florida.

No matter what time of year you visit, you'll be able to find a vacation rental in Longboat Key to suit your needs. In addition to villa rentals with all the amenities and comforts of home, you can also book a beachfront condo rental with white sand beaches right outside your door.

There are also several excellent day-trip options from Longboat Key. Tampa is a short drive via I-75 North. Disney World is also a short distance by car and offers an unforgettable experience for the whole family.

!!!!SUMMER SPECIAL!!!! JULY & AUGUST 2015 - ONLY 1,000 USD/WEEK OR 1,750 USD FOR 2 WEEKS
Feel at home in this spacious waterfront condominium on Longboat Key with luxurious amenities, including heated pool and hot tub with views of the Sarasota Bay, tropical gardens, private boat dock and four lit tennis courts and…

This condo and property is a piece of sunny heaven!

Left on Oct 15, 2014 for a stay in September 2014

The condo was spotless and well equipped with all of our vacation needs. The rooms are spacious and the view is stunning. We will never stay anywhere else when we go to Florida. This condo and location spoiled us! It is 5 star all the way. The pool and grounds are lovely....as are the other people staying there. There are wonderful stores and and restaurants close by. We are already making plans …

$113

Longboat Key Bargain on the beach. Our cozy get away on the beach is a favorite of many guests who enjoy the quiet beachfront. Just a simple beach hideaway for your next quiet stay at the beach It's neat studio apartment with patio and sandy beach at your door. The full size galley kitchen supplies everything you …

You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here in a residential area. One block to the grocery and the trolley stops right in front to take you to St Armands Circle for shopping…

What an amazingly beautiful location for a peaceful stay with a ocean view.

Left on Aug 08, 2014 for a stay in August 2014

We wanted to rent a place with an ocean view in a more relaxing (peaceful) place. We arrived to find our rental had a nice updated cottage feel. Plenty of things to do on Longboat Key. We will definitely return!

$186

Beautifully decorated one bedroom condo directly on the beach. New kitchen with granite counter tops, and a 47in flat screen TV. Watch the sunset from your living room or porch, the sand is only 20 feet from your front door.

Beautiful condo, gorgeous beach... A great value!!

Left on Aug 10, 2013 for a stay in August 2013

My boyfriend and I stayed in this unit August 5th-9th (this past week). The condo is beautiful and was spotless upon our arrival. The private beach and pool right outside our back door was exactly what we had been looking for...

There were several children and teens staying with their parents at the resort while we were there, so we did hear the occasional "screaming child" down at the pool, …

$195

$999/wk August 25-Sept 17 prorated rates . LOWEST of the year ++++++Rated " EXCELLENT" digital badge on TripAdvisor and FlipKey++++++. This exclusive award recognizes outstanding vacation rentals based on reviews of past year so you can rent with confidence…

Best Vacation Ever!!! Can't Wait To Return!!!

Left on Jul 24, 2010 for a stay in May 2010

Our family had the time of our lives here! The kids loved gettting up early, biking then jumping in the pool! The rooms are large and we ate at least one meal in every day because we loved the huge gourmet kitchen!! There was more equipment here than I have in mine!
The owner was easy to work with and always available to take our calls. He also gave great advice on excellent restaurants. We're…

Welcome to your home away from home! Spread out in this beautifully remodeled 3 bedroom top floor unit, soaking in the water views and privacy of the small community of Longboat Landing.
Whether you stay for a few nights, weeks, or months, there is plenty to see and do in between long bouts of well deserved relaxing…

A Perfect Piece of Paradise!

Left on Jun 17, 2014 for a stay in May 2014

My husband and I recently stayed here for a long weekend away. I had never been to Longboat Key previously and could not be happier with our stay!

This rental was plenty of room and then some for the two of us, easily able to accommodate up to eight I would think. The open layout and ability to see right out to the water from the moment of entry was immediately calming. The rental offered …

$269

Florida's SeaHorse Beach Resort on Longboat Key is located on the white sand beaches of the Gulf of Mexico. From the moment you arrive, the friendly and professional staff will welcome you to this Premier property where you can experience a panoramic view of the Gulf from your suite, or while lounging by the heated …

$200

This spectacular two bedroom condominium sits directly fronting on the Gulf in the middle of Long Boat Key. It was recently renovated from floor to ceiling and is beautifully decorated with warm, rich colors. The kitchen has stainless appliances, granite countertops and custom dark polished wood cabinetes. …

$195

This beautifully appointed spacious 1 BR/1BA is recently renovated and with new furniture, tile flooring, and
kitchen upgrades. Enjoy the 180 degree view of the horizon over the beach and the Gulf of Mexico with incredible sunsets. SeaHorse Beach Resort consistently ranks at the top of the rankings of the Small …

$99

*** Ocean Beach Front Special ~ From $99/night or $350/4 nights *** Aug 2-5 , Aug 9-11, Aug 14-26 , Aug 31-Sep 4 , Sep 7-13.
This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from …

$195

Groundfloor Beachfront! From large living and dining area with open kitchen just step outside to your private patio and walk right out to the BEACH (25 seconds!) Magnificent condo with open floor plan, very comfortable for 4-5 people. 2 bedrooms, 2 full bathrooms, ceiling fans, full kitchen, recliner chairs, sleeper …

$329

Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' This beachfront resort is set on beautiful white sand beaches that meet the beautiful turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Rate includes resort fee …

$117

This updated, 2 bedroom and 2 bath condo has sweeping views of the Gulf of Mexico with spectacular sunsets and a quiet beach that stretches for miles. At the north end of Longboat Key, there are plenty of restaurants, shopping and cultural activities nearby. Other amenities include a heated pool, wireless internet, …

Whitney Beach

Left on Apr 19, 2011 for a stay in February 2011

The condo is beautifully funished and fully equipped. The view is unsurpassed and the beach is the best on Longboat Key. A grounds keeper provides just he right level of service. Some others might not like having to use the few stairs, but we prefer the second floor view, which provides a spectacular sunset most days. The pool, beach, and parking lot are all very close. The neighborhood is on the…

$350

Escape to Paradise with Incredible Sunsets and Balmy Breezes direct on the Gulf of Mexico with its beautiful White Sand Beaches stretching for miles. Private and very quiet, and features two bedrooms with a king size bed in the master suite and a queen size bed in the second bedroom, two full baths, updated and newly …

Perfect

Left on Jun 24, 2011 for a stay in February 2011

Great view and location. Longboat Key is a real retreat from reality but a wonderful experience. Tis unit is close to grocery store, drug store, dry cleaner, and many, many good restaurants, from NY Deli to perfect Gulf seafood. Wireless internet a nice surprise.

$169

Our gulf front condominium has a beautiful view of the Gulf of Mexico not only from the balcony, but from the living room as well. We also have two other condos in this same resort that rent at lesser rates than shown below. We only recently purchased this condo, but in 2013 we replaced all the carpet, put in all …

Skip this condo.

Left on Jul 01, 2014 for a stay in May 2014

Check-in at Sand Cay was quick and easy, and the staff was friendly. We could clearly see the improvements the owners have been making, as some furniture and art work were very worn and dated while others were obviously newer. We appreciated the additional amenities the owners were offering, like the stroller, pack and play and coolers, however there was supposed to be a high chair there but we…

$159

NATURAL BEAUTY of Longboat Key
RIGHT ON THE BEACH
PANORAMIC 2ND FLOOR BALCONY VIEWS
On beautiful tropically landscaped Longboat Key, Florida you will find the natural beauty.
Our Studio condo is right on the beach with magnificent panoramic views from its second floor balcony position.
ENJOY THE BEACH FROM YOUR BED…

Loved this condo!

Left on Jan 06, 2014 for a stay in January 2014

My husband and I stayed here with our 2 nieces and loved our stay! We are definitely coming back. The condo was equipped with everything we needed: a nice kitchen, comfortable bed, pullout extra bed for the 2 little girls, and plenty of storage. The best part of our stay was waking up to a gorgeous gulf view. We went for an early morning run and seashell finding trip with the nieces (in early …

$120

LOCATION, LOCATION, LOCATION! Beautiful view of Sarasota Bay with private beach access just across the street. Newly renovated open kitchen and breakfast bar with seating for three, upgraded stainless appliances, and quartz countertops. Entire unit is freshly painted and immaculate with new tile in kitchen and living…

$179

Our condo has everything you will need for a relaxing vacation on the beach.
The island of Longboat Key...
... is one of the most beautiful places in Florida. Longboat was voted the second most favored island in North America, according to a survey by a nationally recognized travel magazine. Daytime excursions are…

$190

SEA PINES This rarely available premier oceanfront location has one of the best views on Longboat Key looking out over the low dunes to the Gulf of Mexico where you can see the dolphins play, and the most amazing sunsets you’ll see anywhere. Quiet and serene with magnificent views, yet only a ten minute drive to …

Wonderful stay at a perfect situated place

Left on Sep 13, 2009 for a stay in August 2009

Our family of 4 (2 adults / 2 teenaged girls)had a wonderful stay at Club Longboat Beach & Tennis. The home had everything we needed even sheets and beachtowels.The kitchen was fully equiped w/pots pans & appliances. Televisions in every bedroom and internet access. The location, just steps to the beach, was perfect. Home is tastefully decorated with all the amenities needed. The pool area is a …

$167

At our beautiful low-rise resort, located directly on the beach, our two-bedroom condominium is fifty paces from the pool and a private beach of soft white sand. 15F in popular Casa del Mar provides a spacious living room/home theatre (46 inch plasma TV & BlueRay Player), vaulted ceilings, and a wall of windows with …

Perfect Vacation -- Quiet, Peaceful, Relaxing -- FUN!!!!!

Left on Sep 29, 2011 for a stay in September 2011

Casa Del Mar is a wonderful vacation resort on the shores of the Gulf of Mexico. The unit that I was in overlooked the pool and had a marvelous view of the beach and Gulf waters which also means that I had a view of an magnificent sunset almost every evening. It was delightfully decorated and had all the amenities of home. The 2 tennis courts are hard-courts that are kept up very well. The pool …

$400

Our luxury vacation home will comfortably accomodate up to 12 guests and is located on a deepwater canal and has a dock suitable for a boat up to 30 feet in length. Beautiful Longboat Key beach is less than a 10 minute walk from the house and world-class shopping and dining at the famous St. Armands Circle is about …

This one-bedroom, ground floor walk-out, has fantastic full gulf views and is only steps to the beach. It features a bright beach decor that will make your vacation in paradise truly memorable. The screened lanai is practically perched upon the sand! An added bonus is that it is a corner unit with extra side …

Perfect Florida vacation spot

Left on May 12, 2014 for a stay in May 2014

This condo was just right for my husband myself and our young 18 mo. old daughter. The space was clean and bright. The resort pool and beach location on the Gulf was ideal. It is not far from St. Armand's Circle or nearby Bradenton Beach or Anna Maria Island. I would recommend this place to anyone as I felt it was comfortable and relaxing.

$250

The Outrigger Resort is a quaint 10 unit complex. This unit is equipted with very comfortable furniture and all your needed appliances and accessories. Included in the kitchen is stove, refrigerator, toaster, coffee pot, etc., including all necessary utensils. The unit is designed with front and rear entries. …

$86

Condo is located in Banyan Bay Club which consists of a total of only 44 units arranged in two floors. This condo is located at the Garden level. No stairs. The lanai at the rear of the unit opens onto a private Banyan and Palm tree-filled lawn with views of Sarasota Bay. The lanai contains a table and seating for …

$167

Available for 3 MONTH MINIMUM rental with approval from condo association.
Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and we have a full …

$225

La Playa is a small 21-unit resort property of privately-owned condominiums available exclusively for weekly rentals twelve-months per year.
Located on spectacular Longboat Key, a short drive from Sarasota on the wide sand beaches of the Gulf of Mexico, La Playa offers privacy and direct beach access not available …

$250

Large Gated Home on waterway - White Sand Beach only steps away.
Our vacation home is spacious and beautifully furnished with 3 bedrooms and a large loft with sleeper-sofa, 3 full bathrooms, sleeps uo to 8 people, Perfect for families or couples. The home has a fully equipped gourmet kitchen with granite counter tops…

loved it!

Left on Mar 04, 2010 for a stay in October 2009

The home was beautiful, all the amenities. Great location. We had no issue at all with the process of renting, made our reservation, paid and went. Everything was smooth, just how you want a vacation home to be. We loved the house itself as well as its proximity to the beach and restaurants/shopping. We would go again, in fact we hope to.

$200

A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. Located in the prestigious yet laid back island of …

$142

Welcome to Longboat Key! This 2 bedroom one bath ground floor condo offers a full kitchen, with open living and dining area. There is a enclosed patio opening to the community pool. Covert Condominiums are located on the northern part of Long Boat Key on Sarasota Bay. There is deeded beach access and walk way across …

Beautiful 2 bedroom condo for rent by owner on Sand Cay beach. Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you need to have an amazing vacation. Please read our reviews, you won't be dissapointed!
The condo is unit 208 at the Sand Cay Beach …

Peaceful and quiet spot on the beach. Your one bedroom vacation home has a private beachfront patio and direct gulf views from the patio, lanai, and bedroom. A full kitchen so you can enjoy meals at sunset instead of fighting the crowd at restaurants. Las Hermanas is just one block from our beautiful new Publix, …

$124

This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here in a residential area…

$110

****Please go to www.longboatbeach.com .**** for more information.
Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit. Best view in the building
A large shopping plaza, Avenue of the Flowers, is behind the complex, offering a large grocery …

Relaxing, rejuvenating, fun

Left on Feb 24, 2011 for a stay in April 2010

We were here for over a week and it was such a nice time. The condo is so cute and the picture above is looking out from the balcony. Shopping and restaurants are fantastic and easily accessible. Big supermarket is within walking distance.

I would highly recommend this vacation rental to all my friends and family.

We have a two bedroom, comfortably furnished condo unit overlooking the Gulf of Mexico. Our favorite room is the lanai - a screened in porch area with dining table and sitting area, especially the views as the sun sets over the Gulf. We are located on the north end of Longboat Key - more secluded and unassuming than …

Want a GREAT, AMAZING, FUN, PERFECT VACATION? Come here!

Left on Aug 13, 2014 for a stay in July 2014

This place is AWESOME, we stayed in the 4 bedroom housebayview with the private pool. It was the perfect vacation. The only mishap was the AC in one of the small rooms stopped working the night b4 we left but never-the-less it was FABULOUS!

$132

Pet friendly, Unique Bungalow Canal Home on the North End of Longboat Key.
Unique Bungalow Canal Home on the North End of Longboat Key.
If you have been putting off writing the next great American novel due to the lack of a peaceful setting then this quaint canal home may be just the place for you. Or perhaps you’ve…

Wonderful and true to Pictures

Left on Mar 18, 2014 for a stay in March 2014

The cottage was well reflected by the pictures. Everything fairly new and clean. Beds comfortable, has everything. Area quiet but short drive to Bradenton and Holmes beaches, for the beach front bars and restuarants. Only petty issue, cable TV, very basic which didn't include ESPN, TBS and some of the other more typical cable stations, so missed some college basketball games leading into March …

$178

Beach in/Beach out Condo (Sleeps 6 - in 2 queen beds and 2 more in a queen sofa bed)
Rarely will you find spectacular beachfront views AND direct walking access to the magnificent white sand beaches of Longboat Key. This “beach in – beach out” condo is just fifty steps from the Gulf of Mexico! Surrounding this …

Quiet & private beach oasis in beautiful LBK

Left on May 15, 2014 for a stay in May 2014

The 1 bedroom condo was very clean and just like posted pictures. 1st floor patio exit to beachfront was nice. I'm used to staying up higher and watching views from a balcony, but this was just as easy and nice to stroll a few hundred feet and sit right on the beach in front of the water. Even though we had rain the entire weekend off and on, our time was spent in local shops, St. Armand Cr and …

$215

Three bedroom cottage available weekly or monthly in the sought after North Longboat Key Village where resident peacocks visit daily. New beds, Linens, towels etc. Also available on VRBO #702686
Offered fully equipped unit reflecting its own unique style of a beach getaway in paradise, full of character, and quaint …

$122

One bedroom one bath very affordable cottages are available weekly or monthly in the eclectic Longbeach Village where resident peacocks visit daily. New Beds, Linens, Towels etc..
Also available on VRBO #706230
Offered FULLY FURNISHED with each unit reflecting its own style of a beach getaway in paradise, full of …

$172

Million Dollar unobstructed ocean views. Right on the beach. Top floor.About a mile north from St Armand Circle.The condo has 2 bedrooms and 2 baths. Kitchen has granite and the place has everything you need.Just bring your clothes and food.Beautiful patio to enjoy the sunset views.Wi-Fi is available.

$175

Charming 1 bedroom 1 bath canal front unit. On canal with dock in the
Back yard. A beautiful Beach, amazing 35 acre park, great restaurants
All within a five minute walk. Great space in an amazing place! Everything you
Need to relax for a long weekend, a week, a month, or a winter, or summer
Season. Leave your …

$173

Magnificent 3 bedroom, 2.5 bath beach front condominium (3 month minimum stay)
The Players Club has all the sophistication and stunning scenery that has made Longboat Key a world class destination. This idyllic location is on the south end of Longboat Key just minutes from downtown Sarasota and St. Armand’s Circle.
…

$121

Spacious corner unit 2 bedrooms 2.5 bathrooms (3 month minimum stay)
The Players Club has all the sophistication and stunning scenery that has made Longboat Key a world class destination. This idyllic luxury beach location is on the south end of Longboat Key just minutes from downtown Sarasota and St. Armand’s …

About Longboat Key

With warm weather year-round and some of the best beaches in the region, Longboat Key has become one of the premiere vacation destinations in the Florida area. Longboat Key has several major festivals and events held throughout the year, so try to plan your trip around one of them. Some of the major events in the area include the St. Armand's Circle Art Festival, held in late January; the Say I Do Again Festival on Valentine's Day, where couples can renew their vows on Siesta Public Beach; and the Siesta Fiesta, an annual arts and crafts fair held in early May.

While you're on vacation in the Longboat Key area, be sure to make time for some of these main attractions and destinations:

-Sarasota Jungle Gardens: There are five shows at the gardens that feature both animals and rare plants.

-Historic Palm Avenue: This is known as downtown Sarasota's "Best Walk in Town."

-Bolletieri Tennis Academy: Located in nearby Bradenton, see the academy where champions like Andre Agassi and Monica Seles got their start.

-Go shopping: St. Armand's Circle has a huge selection of unique shops and fine dining.

-Catch a baseball game: If you're in the area during the spring, the Baltimore Orioles train in nearby Sarasota.

-Historic Spanish Point: Take a guided tour here and learn more about the history of Southwest Florida.

No matter what time of year you visit, you'll be able to find a vacation rental in Longboat Key to suit your needs. In addition to villa rentals with all the amenities and comforts of home, you can also book a beachfront condo rental with white sand beaches right outside your door.

There are also several excellent day-trip options from Longboat Key. Tampa is a short drive via I-75 North. Disney World is also a short distance by car and offers an unforgettable experience for the whole family.

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